[65 Cat 2+2]

I may score as the oldest first car (or at least oldest first car that was also a Pontiac) here.
I was 17 and only driving one year in 1962. I bugged my father for months to let me buy a car. The sales pitch that finally got him to relent was that I would then start paying for my own gas, and promised to continue washing the family car (a new '62 Pontiac Starchief 4-door hardtop).
After much shopping, my choice was between a '57 Belair convertible, or a '58 Bonneville convertible. I chose the Bonneville, mainly because it was Tri-Power equipped and really fast. It was turquoise & white, white top, leather bench seat interior. Wonderbar radio, Speedometer "Cry Baby". Tons of chrome. It had about 35K miles, and I paid $1,000 for it.
What a blast to drive! Spent my time drag racing around the streets of Baltimore. It seems as if at least one or twice a month I'd find myself at the same stoplight as another kid my age who drove a '57 Chrysler Imperial convertible, done all in gray primer (I always thought that was a neat thing to do to a big luxury boat). Our races always were a dead heat. We never met. Weird.
I had that car for 31/2 years. It was rear-ended by a Corvair and totaled - bent frame. Shockingly the little Corvair suffered minor front end damage. I wish I had kept the intake set-up before it went to the junkyard.
I've always missed that car.